Pesticidally active pyridazinone compounds

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.

1 . A compound of the formula (I) 
       
         
           
           
               
               
           
         
         wherein:
 Q is 
 
       
       
         
           
           
               
               
           
         
         
            where the staggered line represents the connection of Q to the rest of compound of the formula (I); 
           A is N or CR Y ; 
           R 1  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 cyanoalkyl, aminocarbonylC 1 -C 6 alkyl, hydroxycarbonylC 1 -C 6 alkyl, C 1 -C 6 nitroalkyl, trimethylsilaneC 1 -C 6 alkyl, C 1 -C 3 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl, C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl wherein the C 3 -C 4 cycloalkyl group is substituted with 1 or 2 halogen atoms, oxetan-3-yl-CH 2 —, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, benzyl, or benzyl substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 6 alkoxy and C 1 -C 6 haloalkyl; 
           R 2a  and R 2b  are independently selected from hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 C 3 haloalkylsuflanyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, NO 2 , SF 5 , CN, C(O)NH 2 , C(O)OH, C(S)NH 2 , C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted with one to three substituents independently selected from R X ; C 1 -C 6 cycloalkylcarbonyl, phenyl, phenyl substituted with one to three substituents independently selected from R X ; heteroaryl, heteroaryl substituted with one to three substituents independently selected from R X ; OR 6 , piperidin-2-one-1-yl, piperidin-2-one-1-yl substituted with one to two substituents independently selected from R X ; pyridin-2-one-1-yl, pyridin-2-one-1-yl substituted with one to two substituents independently selected from R X ; azetidin-1-yl, azetidin-1-yl substituted with one to two substituents independently selected from R X ; pyrrolidin-1-yl, pyrrolidin-1-yl substituted with one to two substituents independently selected from R X ; C 3 -C 6 cycloalkyl-C 1 C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl substituted with one to two substituents independently selected from R Z ; C 3 -C 6 cycloalkyl-C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl-C 1 -C 3 alkoxy substituted with one to two substituents independently selected from R X ; C 1 -C 5 cyanoalkyl, C 1 -C 5 cyanoalkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl substituted with one to three substituents independently selected from R X ; C 1 C 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl substituted with one to three substituents independently selected from R X ; C 1 -C 4 alkylsulfinyl, and C 1 -C 4 alkylsulfinyl substituted with one to three substituents independently selected from R X ; 
           R 3  is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; 
           R 4  is 
         
       
       
         
           
           
               
               
           
         
         
            where the staggered line represents the connection of R 4  to Q a  or Q b ; 
           A 1 , A 2 , and A 3  are, independently of each other, N or CH; 
           R 4c  is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, allyl, propargyl, or C 3 -C 6 cycloalkylC 1 -C 4 alkyl; 
           R 5  is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 alkoxyC(O)—, (C 1 -C 3 alkoxy) 2 CH—, halogen, —CN, NH 2 C(O)—, amino (i.e —NH 2 ), (C 1 -C 3 alkyl)amino, di(C 1 -C 3 alkyl)amino, hydroxy, C 3 -C 4 halocycloalkyl, C 3 -C 4 cyanocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 1 -C 3 alkoxy-C 1 -C 3 alkoxy-C 1 -C 3 alkyl, (C 1 -C 3 alkyl)sulfonylamino, (C 1 -C 3 alkyl)sulfonyl(C 1 -C 3 alkyl)amino, (C 1 -C 3 alkyl)NHC(O)—, (C 1 -C 3 alkyl) 2 NC(O)—, (C 3 -C 4 cycloalkyl)NHC(O)—, (C 3 -C 4 cycloalkyl)(C 1 -C 3 alkyl)NC(O)—, (C 1 -C 3 alkyl)C(O)(C 1 -C 3 alkyl)N—, (C 1 -C 3 alkyl)C(O)NH—, (C 1 -C 3 alkyl)C(O)—, (C 1 -C 3 alkoxy)C(O)—, HC(O)—, diphenylmethanimine, C 1 -C 3 haloalkoxy, phenyl, or a 5-membered heteroaromatic ring; or 
           R 5  is phenyl substituted with one to three substituents selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen, —CN and hydroxyl; or 
           R 5  is a 5-membered heteroaromatic ring substituted with one to three substituents selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen, —CN and hydroxyl; 
           R 5a  and R 5b  are, independently of each other, selected from hydrogen, halogen, —CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, and C 1 -C 3 haloalkoxy; 
           R 6  is phenyl, benzyl, heteroaryl, or C 3 -C 6 cycloalkyl; or 
           R 6  is phenyl, benzyl, heteroaryl, or C 3 -C 6 cycloalkyl, each of which, independently of each other, is substituted with one to three substituents independently selected from R X ; 
           R X  is independently selected from halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, NO 2 , SF 5 , CN, —C(O)NH 2 , —C(S)NH 2 , C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl and C 1 -C 4 alkylsulfonyl; 
           R Y  is selected from hydrogen, C 1 -C 3  alkyl, C 1 -C 3 haloalkyl, hydroxy, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, —CN and cyclopropyl; 
           R Z  is selected from oxo, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy and CN; 
           X 0  is O or S; and 
         
         an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula I. 
       
     
     
         2 . The compound according to  claim 1 , wherein A is N or CH. 
     
     
         3 . The compound according to  claim 1 , wherein R 4  is R 4a , and
 A 1  is N, A 2  is N or CH, and A 3  is N or CH; or   A 1  is N, A 2  is N or CH, and A 3  is CH; or   A 1  is N, A 2  is CH, and A 3  is N or CH; or   A 1  is N, A 2  is CH, and A 3  is CH: or   A 1  or A 2  is N, the other is N or CH, and A 3  is CH; or   A 1  or A 2  is N, the other is CH, and A3 is CH.   
     
     
         4 . The compound according to  claim 1 , wherein R 4  is R 4b , and A 1  is N or CH. 
     
     
         5 . The compound according to  claim 1 , wherein R 4c  is methyl, ethyl, propyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, allyl, propargyl, cyclopropylmethyl, cyclobutylmethyl, 2-cyclpropylethyl, or 3-cyclopropylpropyl; preferably R 4  is methyl, ethyl, or 2,2-difluoroethyl. 
     
     
         6 . The compound according to  claim 1 , wherein X 0  is O. 
     
     
         7 . The compound according to  claim 1 , wherein R 1  is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, cyclopropyl-methyl, allyl, propargyl, benzyloxycarbonyl, or benzyl; preferably R 1  is hydrogen, or methyl. 
     
     
         8 . The compound according to  claim 1 , wherein R 2a  is halogen, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkylsulfanyl, C 1 -C 3 haloalkoxy, C 3 -C 6 cycloalkyl optionally substituted with one or two substituents independently selected from C 1 -C 3 haloalkyl, cyano and halogen, C 3 -C 6 cycloalkylC 1 -C 4 alkyl optionally substituted with one to three substituents independently selected from C 1 -C 3 haloalkyl, cyano and halogen, C 1 -C 5 cyanoalkyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 3 -C 6 cycloalkylsulfanyl, C 3 -C 6 cycloalkylsulfinyl, or C 3 -C 6 cycloalkylsulfonyl; preferably chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylsulfonyl, trifluoromethylsulfonyl, cyanoisopropyl, or cyanocyclopropyl. 
     
     
         9 . The compound according to  claim 1 , wherein R 2b  is halogen, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkylsulfanyl, C 1 -C 3 haloalkylsulfonyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, or CN: preferably R 2b  is chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, or difluoromethoxy. 
     
     
         10 . The compound according to  claim 1 , wherein R 3  is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl, preferably R 3  is methyl. 
     
     
         11 . The compound according to  claim 1 , wherein
 when Q is Q a : R 5  is hydrogen, methyl, trifluoromethoxy, methoxy, cyclopropyl, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, difluoromethoxy, 2,2,2-trifluoroethyl, chloro, bromo, methoxyethoxy, methylcarbonyl or methoxycarbonyl; and   when Q is Q b : R 5a  is hydrogen, halogen, CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy; and R 5b  is hydrogen, halogen, CN, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy.   
     
     
         12 . A composition comprising a compound as defined in  claim 1 , one or more auxiliaries and diluent, and optionally one or more other active ingredient. 
     
     
         13 . A method
 (i) of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound as defined in  claim 1 ; or   (ii) for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a compound as defined in  claim 1 ; or   (iii) of controlling parasites in or on an animal in need thereof comprising administering an effective amount of a compound as defined in  claim 1 .   
     
     
         14 . A plant propagation material, such as a seed, comprising, or treated with or adhered thereto, a compound as defined in  claim 1 . 
     
     
         15 . A compound of the formula XII(i), or a tautomer thereof, 
       
         
           
           
               
               
           
         
         wherein A 1 , A 2 , A 3  and R 4c  are as defined in  claim 1 , provided said compound is not 
       
       
         
           
           
               
               
           
         
         6-hydrazinyl-2-methyl-3(2H)-pyridazinone, nor 
       
       
         
           
           
               
               
           
         
         6-hydrazinyl-2-ethyl-3(2H)-pyridazinone, nor a tautomer thereof. 
       
     
     
         16 . A compound of the formula XX(i), XXI(i) or XXII(i) 
       
         
           
           
               
               
           
         
         wherein R 4a  is as defined in  claim 1 ; and wherein X −  is an anion selected from the conjugate base of an inorganic acid selected from hydrochloric acid, hydrobromic acid, hydrogen fluoride, hydrogen iodide, sulfuric acid, or the conjugate base of an organic acid selected from a carboxylic acid or a sulfonic acid.